4-bromo-2-fluoro-1-(methylsulfonylmethyl)benzene

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 4-bromo-2-fluoro-1-(methylsulfonylmethyl)benzene (2 g, 7.487 mmol) in dimethylformamide (11 mL) were added ethyl 2-chloropropionate (1.24 mL, 9.733 mmol), manganese (822 mg, 14.974 mmol) and (2,2′-bipyridine)nickel(II)-dibromide (196 mg, 0.524 mmol). Trifluoroacetic acid (4 drops) was added. The reaction mixture was stirred overnight at 60° C. After cooling down to room temperature, the mixture was hydrolyzed by 1N HCl (30 mL) and extracted with ethyl acetate (3×50 mL). The organic layer was dried over magnesium sulfate and filtered. The solvent was removed in vacuo. The crude product was purified by CC (eluent: ethyl acetate/cyclohexane (1:1)) to give ethyl 2-(3-fluoro-4-(methylsulfonylmethyl)phenyl)propanoate (966 mg, 45%). After cooling down to room temperature extracted with ethyl acetate (3×50 mL) The organic layer was dried over magnesium sulfate filtered The solvent was removed in vacuo The crude product was purified by CC (eluent: ethyl acetate/cyclohexane (1:1))